【作者】 陈孝云；

【导师】 郭庆祥；

【作者基本信息】 中国科学技术大学 ， 有机化学， 2010， 硕士

【摘要】 首先概述了用于络合和光解释放生物活性小分子的双光子光敏基团和双光子性质的金属离子探针(主要是Zn2+探针)的发展。鉴于目前人们对生物体中功能小分子(如:谷氨酸等)和功能离子(如Zn2+、Mg2+等)在生物体中功能研究的迫切需要,我们设计合成了一系列双光子光敏基团和具有探测生物功能金属离子的探针(主要是Zn2+的探针)。并且研究了这类光敏基团的物理化学性质及其对生物活性小分子的络合和光解释放的能力。同时,研究了离子探针对金属离子光学性质、对金属离子的选择性、检测的灵敏度等。本论文的主要目的是发展基于喹啉的金属Zn2+的双光子荧光探针,并努力实现其在活性细胞中的应用。通过改变喹啉环上的供电子基团的种类及位置来合成一系列新的喹啉衍生物,以用于络合和光解释放生物活性物质,如谷氨酸等。对其常规性质进行研究,并根据研究结果来分析这类光敏基团作为双光子光敏基团的性质,并作为参考用于发展性质更加优良的双光子光敏基团。这些实验结果对于今后的工作有很大的参考指导作用。此外,还开发了支链不参与金属离子配位的、简单的、喹啉衍生的、可用双子技术激发的Zn2+荧光探针,并研究了该Zn2+探针在双光子技术激发下(λex=800nm),在活性细胞中的实际应用。这一研究的成功拓宽了双光子技术在生物学研究中的应用领域。同时,也给今后的金属离子探针的发展提供了参考。更多还原

【Abstract】 The metal ion probes are indispensable for studying the roles of small biological molecules (such as glutamic acid) and ions (such as Zn2+ and Mg2+) played in various biological processes. We first reviewed the recent development of two-photon probes of metal ions (mainly Zn2+ probes) and the photosensitive groups capable of caging and photo-releasing the bioactive small molecules. Afterwards, a series of photosensitive groups and two-photon probes of functional metal ions (mainly Zn2+ probes) designed by our group has been presented. Their physicochemical properties and abilities to cage and photo-release the bioactive small molecules were studied. And the optical properties, metal-ion selectivity and detection sensitivity of these metal ion probes were also investigated. The main purpose of our efforts is to develop the quinoline-based two-photon probes of Zn(II) and to realize their applications in living cells.By changing the positions and the properties of electron donating groups attached to the quinoline ring, we synthesized a series of new quinoline derivatives capable of caging and photo-releasing the bioactive small molecules, such as glutamic acid etc. Then a series of studies have been conducted to reveal the two-photon absorbing ability of these photosensitive groups and their potential to be used in two-photon metal ion probes. Furthermore, a new and simple 7-substituted quinoline-based two-photon probes of Zn(II) has been developed. Unlike previously reported 8-substituted quinoline-based probes, the electron donating group attached to quinoline ring did not participate in the interaction with metal ion. Finally, the application of this newly developed two-photon probes in living cells has been tested (λex=800nm). These studies are of crucial importance for the application of two-photon technology in biological systems and will provide a good reference to the development of metal ion probes.更多还原